# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zxq-1-3_auto
_database_code_depnum_ccdc_archive 'CCDC 2322455'
loop_
_audit_author_name
_audit_author_address
'xinqin zhang'
;jiangxi normal university
China
;
_audit_update_record             
;
2023-12-29 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.33(C32 H28 N2 O2 Se)'
_chemical_formula_sum            'C10.67 H9.33 N0.67 O0.67 Se0.33'
_chemical_formula_weight         183.84
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.5627(11)
_cell_length_b                   14.7048(7)
_cell_length_c                   14.8441(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2742.2(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4710
_cell_measurement_theta_min      3.8940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16662
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.521
_diffrn_reflns_theta_min         3.476
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0706
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  42.00   1.00   19.66    --   16.70  77.00 -90.00   52
  2  ω    -15.00  55.00   1.00   19.66    --   16.70 -99.00  90.00   70
  3  ω     -3.00  86.00   1.00   19.66    --   16.70  37.00 150.00   89
  4  ω    -45.00  16.00   1.00   19.66    --  -15.76  19.00-120.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0337244000
_diffrn_orient_matrix_UB_12      0.0306929000
_diffrn_orient_matrix_UB_13      0.0232195000
_diffrn_orient_matrix_UB_21      -0.0410264000
_diffrn_orient_matrix_UB_22      -0.0331562000
_diffrn_orient_matrix_UB_23      0.0002743000
_diffrn_orient_matrix_UB_31      0.0191048000
_diffrn_orient_matrix_UB_32      -0.0169090000
_diffrn_orient_matrix_UB_33      0.0417749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                4030
_reflns_number_total             6380
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         6380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0981
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.006(12)
 -0.006(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C00R(H00R)
3.b Secondary CH2 refined with riding coordinates:
 C00I(H00B,H00C)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K), C00M(H00M), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
3.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
3.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.30836(5) 0.57060(3) 0.38440(3) 0.0643(2) Uani 1 1 d . . . . .
O002 O 0.5474(3) 0.6195(2) 0.3170(2) 0.0576(9) Uani 1 1 d . . . . .
H002 H 0.560818 0.565554 0.325111 0.086 Uiso 1 1 calc GR . . . .
N003 N 0.3425(3) 0.7875(2) 0.2035(2) 0.0384(9) Uani 1 1 d . . . . .
O004 O 0.2926(4) 0.6774(2) 0.10227(19) 0.0732(12) Uani 1 1 d . . . . .
N005 N 0.4053(3) 0.9312(2) 0.1558(2) 0.0436(9) Uani 1 1 d . . . . .
C006 C 0.4027(4) 0.9004(3) 0.0664(3) 0.0420(12) Uani 1 1 d . . . . .
C007 C 0.3068(4) 0.7297(3) 0.2776(3) 0.0410(10) Uani 1 1 d . . . . .
C008 C 0.3878(4) 0.9073(3) 0.3135(3) 0.0370(11) Uani 1 1 d . . . . .
C009 C 0.4115(4) 0.9756(3) 0.4872(3) 0.0508(13) Uani 1 1 d . . . . .
C00A C 0.4554(4) 0.8655(3) 0.3737(3) 0.0496(12) Uani 1 1 d . . . . .
H00A H 0.492741 0.813678 0.356599 0.060 Uiso 1 1 calc R . . . .
C00B C 0.3611(4) 0.6548(3) 0.2953(3) 0.0447(12) Uani 1 1 d . . . . .
C00C C 0.3780(4) 0.8752(3) 0.2191(3) 0.0386(11) Uani 1 1 d . . . . .
C00D C 0.3332(4) 0.9843(3) 0.3402(3) 0.0453(12) Uani 1 1 d . . . . .
H00D H 0.289130 1.014437 0.299700 0.054 Uiso 1 1 calc R . . . .
C00E C 0.1119(5) 0.7997(3) 0.4578(4) 0.0631(16) Uani 1 1 d . . . . .
H00E H 0.110616 0.808076 0.519900 0.076 Uiso 1 1 calc R . . . .
C00F C 0.4676(5) 0.9006(3) 0.4594(3) 0.0553(14) Uani 1 1 d . . . . .
H00F H 0.514730 0.872787 0.499119 0.066 Uiso 1 1 calc R . . . .
C00G C 0.3441(4) 1.0165(3) 0.4274(3) 0.0559(15) Uani 1 1 d . . . . .
H00G H 0.304784 1.066854 0.445602 0.067 Uiso 1 1 calc R . . . .
C00H C 0.3007(5) 0.4647(3) 0.3087(4) 0.0595(14) Uani 1 1 d . . . . .
C00I C 0.4655(4) 0.6278(3) 0.2520(3) 0.0501(13) Uani 1 1 d . . . . .
H00B H 0.456656 0.570205 0.220963 0.060 Uiso 1 1 calc R . . . .
H00C H 0.485551 0.673184 0.207740 0.060 Uiso 1 1 calc R . . . .
C00J C 0.0226(5) 0.8149(4) 0.4081(4) 0.0699(17) Uani 1 1 d . . . . .
H00J H -0.040300 0.831780 0.436666 0.084 Uiso 1 1 calc R . . . .
C00K C 0.4412(5) 0.9574(3) -0.0004(3) 0.0589(14) Uani 1 1 d . . . . .
H00K H 0.466387 1.014949 0.014442 0.071 Uiso 1 1 calc R . . . .
C00L C 0.3678(4) 0.8129(3) 0.0446(3) 0.0438(12) Uani 1 1 d . . . . .
C00M C 0.2047(5) 0.7716(3) 0.4158(3) 0.0527(13) Uani 1 1 d . . . . .
H00M H 0.265098 0.760115 0.450203 0.063 Uiso 1 1 calc R . . . .
C00N C 0.3309(4) 0.7523(3) 0.1147(3) 0.0462(11) Uani 1 1 d . . . . .
C00O C 0.2085(4) 0.7604(3) 0.3228(3) 0.0429(12) Uani 1 1 d . . . . .
C00P C 0.4423(5) 0.9289(4) -0.0886(3) 0.0688(16) Uani 1 1 d . . . . .
H00P H 0.466834 0.967745 -0.133515 0.083 Uiso 1 1 calc R . . . .
C00Q C 0.4074(5) 0.8435(4) -0.1104(3) 0.0681(16) Uani 1 1 d . . . . .
H00Q H 0.409113 0.824691 -0.170222 0.082 Uiso 1 1 calc R . . . .
C00R C 0.4232(6) 1.0136(4) 0.5823(3) 0.0777(19) Uani 1 1 d . . . . .
H00R H 0.379403 1.068760 0.582559 0.093 Uiso 1 1 calc R . . . .
C00S C 0.3698(5) 0.7850(3) -0.0452(3) 0.0586(15) Uani 1 1 d . . . . .
H00S H 0.345872 0.727274 -0.061006 0.070 Uiso 1 1 calc R . . . .
C00T C 0.2691(5) 0.4701(4) 0.2203(4) 0.0772(18) Uani 1 1 d . . . . .
H00T H 0.252782 0.526323 0.195114 0.093 Uiso 1 1 calc R . . . .
C00U C 0.3228(5) 0.3811(3) 0.3469(4) 0.0774(18) Uani 1 1 d . . . . .
H00U H 0.343928 0.376820 0.406791 0.093 Uiso 1 1 calc R . . . .
C00V C 0.0249(5) 0.8056(4) 0.3159(4) 0.0679(16) Uani 1 1 d . . . . .
H00V H -0.035824 0.817806 0.282151 0.082 Uiso 1 1 calc R . . . .
C00W C 0.1172(5) 0.7780(3) 0.2733(4) 0.0580(14) Uani 1 1 d . . . . .
H00W H 0.118084 0.771251 0.211021 0.070 Uiso 1 1 calc R . . . .
C00X C 0.3126(7) 0.3017(4) 0.2928(6) 0.101(3) Uani 1 1 d . . . . .
H00X H 0.326266 0.244662 0.317112 0.121 Uiso 1 1 calc R . . . .
C00Y C 0.2827(7) 0.3100(6) 0.2056(7) 0.121(4) Uani 1 1 d . . . . .
H00Y H 0.276640 0.257915 0.170387 0.145 Uiso 1 1 calc R . . . .
C00Z C 0.2616(6) 0.3918(5) 0.1684(5) 0.098(2) Uani 1 1 d . . . . .
H00Z H 0.242085 0.395646 0.108056 0.118 Uiso 1 1 calc R . . . .
C010 C 0.3757(9) 0.9555(7) 0.6496(4) 0.164(4) Uani 1 1 d . . . . .
H01A H 0.308915 0.932752 0.627717 0.246 Uiso 1 1 calc GR . . . .
H01B H 0.364026 0.989746 0.703810 0.246 Uiso 1 1 calc GR . . . .
H01C H 0.422515 0.905511 0.662097 0.246 Uiso 1 1 calc GR . . . .
C011 C 0.5284(7) 1.0449(10) 0.5989(6) 0.218(7) Uani 1 1 d . . . . .
H01D H 0.573985 0.993934 0.610652 0.326 Uiso 1 1 calc GR . . . .
H01E H 0.528203 1.084742 0.650150 0.326 Uiso 1 1 calc GR . . . .
H01F H 0.553989 1.077335 0.547081 0.326 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C00B 1.929(4) . ?
Se01 C00H 1.923(5) . ?
O002 C00I 1.415(6) . ?
N003 C007 1.460(5) . ?
N003 C00C 1.385(5) . ?
N003 C00N 1.424(5) . ?
O004 C00N 1.216(5) . ?
N005 C006 1.402(5) . ?
N005 C00C 1.296(5) . ?
C006 C00K 1.386(6) . ?
C006 C00L 1.397(6) . ?
C007 C00B 1.322(6) . ?
C007 C00O 1.475(7) . ?
C008 C00A 1.376(6) . ?
C008 C00C 1.484(6) . ?
C008 C00D 1.382(6) . ?
C009 C00F 1.372(6) . ?
C009 C00G 1.366(7) . ?
C009 C00R 1.525(6) . ?
C00A C00F 1.382(6) . ?
C00B C00I 1.514(7) . ?
C00D C00G 1.385(6) . ?
C00E C00J 1.361(8) . ?
C00E C00M 1.384(7) . ?
C00H C00T 1.373(7) . ?
C00H C00U 1.382(7) . ?
C00J C00V 1.377(8) . ?
C00K C00P 1.375(6) . ?
C00L C00N 1.446(6) . ?
C00L C00S 1.395(6) . ?
C00M C00O 1.392(6) . ?
C00O C00W 1.387(7) . ?
C00P C00Q 1.369(7) . ?
C00Q C00S 1.379(7) . ?
C00R C010 1.445(10) . ?
C00R C011 1.420(10) . ?
C00T C00Z 1.390(8) . ?
C00U C00X 1.423(8) . ?
C00V C00W 1.381(7) . ?
C00X C00Y 1.352(10) . ?
C00Y C00Z 1.350(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00H Se01 C00B 97.8(2) . . ?
C00C N003 C007 121.0(3) . . ?
C00C N003 C00N 121.7(3) . . ?
C00N N003 C007 117.1(3) . . ?
C00C N005 C006 118.3(4) . . ?
C00K C006 N005 118.3(4) . . ?
C00K C006 C00L 120.0(4) . . ?
C00L C006 N005 121.6(4) . . ?
N003 C007 C00O 114.9(3) . . ?
C00B C007 N003 118.4(4) . . ?
C00B C007 C00O 126.6(4) . . ?
C00A C008 C00C 121.4(4) . . ?
C00A C008 C00D 119.1(4) . . ?
C00D C008 C00C 119.3(4) . . ?
C00F C009 C00R 121.6(5) . . ?
C00G C009 C00F 118.5(4) . . ?
C00G C009 C00R 119.9(5) . . ?
C008 C00A C00F 119.9(4) . . ?
C007 C00B Se01 119.6(4) . . ?
C007 C00B C00I 125.6(4) . . ?
C00I C00B Se01 114.9(3) . . ?
N003 C00C C008 118.8(4) . . ?
N005 C00C N003 123.8(4) . . ?
N005 C00C C008 117.4(4) . . ?
C008 C00D C00G 119.9(4) . . ?
C00J C00E C00M 119.9(5) . . ?
C009 C00F C00A 121.3(4) . . ?
C009 C00G C00D 121.2(5) . . ?
C00T C00H Se01 121.8(4) . . ?
C00T C00H C00U 120.1(5) . . ?
C00U C00H Se01 118.1(4) . . ?
O002 C00I C00B 111.3(4) . . ?
C00E C00J C00V 120.3(6) . . ?
C00P C00K C006 120.1(5) . . ?
C006 C00L C00N 120.0(3) . . ?
C00S C00L C006 119.2(4) . . ?
C00S C00L C00N 120.8(4) . . ?
C00E C00M C00O 120.7(6) . . ?
N003 C00N C00L 114.2(3) . . ?
O004 C00N N003 120.6(4) . . ?
O004 C00N C00L 125.1(4) . . ?
C00M C00O C007 121.1(5) . . ?
C00W C00O C007 120.6(4) . . ?
C00W C00O C00M 118.3(5) . . ?
C00Q C00P C00K 120.1(5) . . ?
C00P C00Q C00S 121.1(4) . . ?
C010 C00R C009 112.6(5) . . ?
C011 C00R C009 111.7(6) . . ?
C011 C00R C010 117.1(8) . . ?
C00Q C00S C00L 119.5(4) . . ?
C00H C00T C00Z 120.1(6) . . ?
C00H C00U C00X 118.7(6) . . ?
C00J C00V C00W 120.1(6) . . ?
C00V C00W C00O 120.5(5) . . ?
C00Y C00X C00U 119.5(7) . . ?
C00Z C00Y C00X 121.7(7) . . ?
C00Y C00Z C00T 119.9(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.259
_oxdiff_exptl_absorpt_empirical_full_min 0.597
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.006(12)
2 -0.006(12)

